53928-30-6

Basic information

• Product Name: 1,2-O-ISOPROPYLIDENE-3,5,6-TRI-O-BENZYL-ALPHA-D-GLUCOFURANOSE
• Synonyms: 1,2-O-ISOPROPYLIDENE-3,5,6-TRI-O-BENZYL-ALPHA-D-GLUCOFURANOSE;3,5,6-tri-O-.benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose;1-O,2-O-(1-Methylethylidene)-3-O,5-O,6-O-tris(phenylmethyl)-α-D-glucofuranose;1-O,2-O-Isopropylidene-3-O,5-O,6-O-tribenzyl-α-D-glucofuranose;Einecs 258-868-3;Tri-O-benzyl-a-D-monoacetoneglucofuranose;3,5,6-Tri-O-benzyl-1,2-O-Isopropylidene-a-D-glucofuranose;3,5,6-tri-O-Benzyl-1,2-O-(1-methylethyldiene)-α-D-glucofuranose
• CAS NO: 53928-30-6
• Molecular Formula: C₃₀H₃₄O₆
• Molecular Weight: 490.58736
• EINECS: 258-868-3
• Mol File: 53928-30-6.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 589.7 °C at 760 mmHg
• Flash Point: 228 °C
• Appearance: /
• Density: 1.2 g/cm³
• Vapor Pressure: 2.89E-13mmHg at 25°C
• Refractive Index: 1.594
• CAS DataBase Reference: 1,2-O-ISOPROPYLIDENE-3,5,6-TRI-O-BENZYL-ALPHA-D-GLUCOFURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-ISOPROPYLIDENE-3,5,6-TRI-O-BENZYL-ALPHA-D-GLUCOFURANOSE(53928-30-6)
• EPA Substance Registry System: 1,2-O-ISOPROPYLIDENE-3,5,6-TRI-O-BENZYL-ALPHA-D-GLUCOFURANOSE(53928-30-6)

Safety Data

• Hazardous Substances Data: 53928-30-6(Hazardous Substances Data)

Usage

Uses

1,2-O-Isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranose can be used in cancer treatment as it exhibits antitumor and antiproliferative activity.

InChI:InChI=1/C30H34O6/c1-30(2)35-28-27(33-20-24-16-10-5-11-17-24)26(34-29(28)36-30)25(32-19-23-14-8-4-9-15-23)21-31-18-22-12-6-3-7-13-22/h3-17,25-29H,18-21H2,1-2H3/t25-,26-,27+,28-,29-/m1/s1

Upstream product

• 100-39-0 benzyl bromide 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 100-44-7 benzyl chloride 

Downstream Products

• 959925-62-3 allyl 3,5,6-tri-O-benzyl-α-D-glucofuranoside 
• 81823-12-3 1,2-O-isopropylidene-3,6-di-O-benzyl-α-D-glucofuranose 
• 35958-64-6 3,5,6-Tri-O-benzyl-α,β-D-glucofuranose 
• 20822-88-2 methyl 3,5,6,-tri-O-benzyl-α-D-glucofuranoside 
• 20822-89-3 methyl 3,5,6,-tri-O-benzyl-β-D-glucofuranoside 
• 4132-40-5 2-O-Methyl-D-glucose 

Relevant articles and documents

Synthesis and antimicrobial activity of (?)-cleistenolide and analogues

Using the “chiral pool” approach, two modified total syntheses of the biologically active δ-lactone cleistenolide (1) have been achieved starting from D-glucose. These approaches also enabled the preparation of novel analogues and derivatives of natural product 1. The applied strategy for the synthesis of 1 involves: the initial degradation of the chiral precursor for a single C-atom, C2-fragment chain extension using Z-selective Wittig reaction, and the final δ-lactonization. All tested cleistenolide analogues displayed antimicrobial activity against a panel of nine microbial strains, most of them superseding the activity of cleistenolide itself, and, in some cases, coming close in value to the observed minimal inhibitory concentrations of chloramphenicol. Increased lipophilicity of the derivatives and the non-sterically congested conjugated lactone moiety were a prerequisite for analogues with high inhibitory activity against S. aureus and, in general, Gram-positive bacteria.

New antitumour agents with α,β-unsaturated δ-lactone scaffold: Synthesis and antiproliferative activity of (?)-cleistenolide and analogues

A stereoselective total synthesis of (?)-cleistenolide (1) from D-glucose has been achieved. This new approach for the synthesis of (?)-cleistenolide and analogues involves a one-C-atom degradation of the chiral precursor, (Z)-selective Wittig olefination, followed by the final δ-lactonisation. Synthesized compounds showed potent growth inhibitory effects against selected human tumour cell lines, especially 2,4,6-trichlorobenzoyl derivative 12, which in the culture of MDA-MB 231 cells displayed the highest activity (IC500.02?μM) of all compounds under evaluation. A preliminary SAR study reveals the structural features that are beneficial for antiproliferative activity of synthesized δ-lactones, such as presence of either electron-withdrawing or electron-donating substituents in the aromatic ring, as well as the presence of cinnamoyl functionality instead of benzoyl group at the O-7 position.

First synthesis of 4a-carba-β-d-galactofuranose

The synthesis of 4a-carba-β-d-galactofuranose is described starting from diacetone glucose. The key ring-closure step was carried out by metathesis to form a cyclopentene. Catalytic hydrogenation of the C{double bond, long}C double bond gave the galacto configured saturated carbahexofuranose with excellent diastereoselectivity.